Ethanol → 2-(4-Acetylaminophenoxy)ethyl 2,6-dimethyl-5-(2-isopropylthioethoxycarbonyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate

HRID 4583

Reaktionsgleichung

Reaktionsgleichung von HRID 4583
[N+:1]([C:4]1[CH:5]=[C:6](C=C[CH:30]=1)[CH:7]=[CH:8][C:9]([CH2:11][C:12]([O:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:20][CH:19]=1)=[O:13])=O)([O-:3])=[O:2].[NH2:31]/[C:32](/[CH3:43])=[CH:33]\[C:34]([O:36][CH2:37][CH2:38][S:39][CH:40]([CH3:42])[CH3:41])=[O:35].[CH2:44](O)[CH3:45]>>[CH3:44][C:45]1[NH:31][C:32]([CH3:43])=[C:33]([C:34]([O:36][CH2:37][CH2:38][S:39][CH:40]([CH3:41])[CH3:42])=[O:35])[CH:9]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:30]=2)[C:11]=1[C:12]([O:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:27])[CH3:26])=[CH:22][CH:23]=1)=[O:13]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 573157372-(4-Acetylaminophenoxy)ethyl 2-(3-nitrobenzylidene)acetylacetateHCID 867414092-Isopropylthioethyl 3-aminocrotonate

Produkt 1

HCID 201512182-(4-Acetylaminophenoxy)ethyl 2,6-dimethyl-5-(2-isopropylthioethoxycarbonyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylateAusbeute 42 %

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

12 g (0l03 moles) of 2-(4-acetylaminophenoxy)ethyl 2-(3-nitrobenylidene)acetylacetate and 5.92 g (0.03 moles) of 2-isopropylthioethyl 3-aminocrotonate are heated under reflux in 30 ml of ethanol for 8 hours. The solution is then cooled to -5° C. to obtain 2-(4-acetylaminophenoxy)ethyl 2,6-dimethyl-5-(2-isopropylthioethoxycarbonyl)-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate as yellow crystals melting--after recrystallisation in aqueus ethanol--at 142°-144° C. The yield was 42% of the theoretical yield.

Quellen und Nachweise

ORD-Eintrag
ord-d3063e5ebfc341bb90d8962965943e78
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727066

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